Do you need to create any managed paths in your VM farm?

After you copied the databases over the to VM farm did you detach and
attach them in SharePoint?

No custom managed paths need to be created. All of my sites are using the
/sites managed path.

I've also tried detaching the content databases while trying attach them both in
the GUI as well as through stsadm -o addcontentdb but it doesn't seem to make a
difference in access the initial page of the site.

The "initial page of the site?" Are other pages working? Did the VM
farm work before you attached these databases? Are your AAMs set
correctly?

What I mean by initial page is that whenever you point to the entry point of any
of the sites that have the issue (e.g.http://blahblah/sites/newsite), I
encounter the 404 with a browser address of http://
blahblah/_layouts/spsredirect.aspx?OldUrl=http://blah/ sites/ originalsite
Any deeper links such as Site Settings, Documents, etc. seem to display
properly.

Everything else on the VM farm seems to be fine. I had created web applications
with dummy content databases before attaching the content databases with the
restored content. The one thing I'm thinking about, though, would be to create
new databases in that web application and then restoring directly to that
database rather than attaching "foreign" content databases.

As far as AAM's go, we didn't have any special AAM's set so I didn't think I
needed to do anything differently here.

Are either of the environments in the middle of an upgrade? Does this
help?
stsadm.blogspot.com/.../...3-area-url-mappings.htm
l

We did a gradual upgrade last year. I'll give that entry a try tomorrow but I'm
not too confident. That seems to address old bucket web URL's and these are
just top-level site collections.

Did you finalize the upgrade when you were finished?

Yes, the originating farm was finalized back in January. The custom STSADM
extention comes back with the following error:

Source web application does not contain an Upgrade Area URL Mapping list.

This makes sense since the VM farm wouldn't have any awareness of upgrade
activity in the past.

Just as an experiment, I've also completed a STSADM backup/delete/restore to see
if the site would work properly but no luck there.